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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H36O6
Molecular Weight 456.5711
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTRIOL TRIPROPIONATE

SMILES

[H][C@@]12C[C@@H](OC(=O)CC)[C@H](OC(=O)CC)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(OC(=O)CC)C=C4

InChI

InChIKey=ONMZMZJEZHMWQL-REUUDLSRSA-N
InChI=1S/C27H36O6/c1-5-23(28)31-17-9-11-18-16(14-17)8-10-20-19(18)12-13-27(4)21(20)15-22(32-24(29)6-2)26(27)33-25(30)7-3/h9,11,14,19-22,26H,5-8,10,12-13,15H2,1-4H3/t19-,20-,21+,22-,26+,27+/m1/s1

HIDE SMILES / InChI

Molecular Formula C27H36O6
Molecular Weight 456.5711
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Estriol tripropionate (brand name Estriel), or estriol tripropanoate, is semisynthetic, steroidal estrogen. Estriol is a safe estrogen hormone that has been used for decades in Europe to treat hot flashes and vaginal dryness. Estriol is a major urinary estrogen. During pregnancy, large amount of estriol is produced by the placenta. Isomers with inversion of the hydroxyl group or groups are called epiestriol. Though estriol is used as part of the primarily North American phenomenon of bioidentical hormone replacement therapy, it is not approved for use by the FDA or Health Canada. It is however available in the United States by prescription filled only by compounding pharmacies. It has also been approved and marketed throughout Europe and Asia for approximately 40 years for the treatment of post-menopausal hot flashes. It is an estrogen receptor agonist.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
250.0 pM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Ovestin 1 mg cream
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
ESTRIOL TRIPROPIONATE (Estriol) contains 1mg estriol in 1g cream. Use the applicator to apply the cream in the vagina. The applicator has a ring marked on the body. Fill the applicator up to the ring mark with Ovestin cream to get the correct dose. 1. Remove the cap from the tube and turn it upside down. Then use the sharp point to open the tube. 2. Screw the end of the applicator onto the tube. 3. Squeeze the tube to fill the applicator with the cream up to the red ring mark (the plunger will stop at the ring mark). 4. Unscrew applicator from the tube and put the cap back on the tube. 5. To apply the cream, lie down, put the end of the applicator deep into the vagina and slowly push plunger all the way in.
Route of Administration: Vaginal
In Vitro Use Guide
Incubation of the neutrophils in HBSS both with 30 nM Estriol (Estriol tripropionate) resulted in the synthesis of 1.8 ngm maspin with simultaneous increase of NO synthesis
Substance Class Chemical
Record UNII
S2A0P1AFQ9
Record Status Validated (UNII)
Record Version